CA1070335A - Resines derivees d'hydrocarbures de la piperylene et d'olefines tertiaires ramifiees a substituants methyle - Google Patents
Resines derivees d'hydrocarbures de la piperylene et d'olefines tertiaires ramifiees a substituants methyleInfo
- Publication number
- CA1070335A CA1070335A CA233,226A CA233226A CA1070335A CA 1070335 A CA1070335 A CA 1070335A CA 233226 A CA233226 A CA 233226A CA 1070335 A CA1070335 A CA 1070335A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- hydrocarbon
- piperylene
- weight percent
- butene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000011347 resin Substances 0.000 title claims abstract description 73
- 229920005989 resin Polymers 0.000 title claims abstract description 73
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 38
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 37
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 title claims abstract description 35
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 7
- -1 olefin hydrocarbons Chemical group 0.000 title description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims abstract description 22
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001336 alkenes Chemical group 0.000 claims abstract description 16
- 229910015900 BF3 Inorganic materials 0.000 claims abstract description 12
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 34
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 28
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 16
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000005673 monoalkenes Chemical class 0.000 claims description 9
- 244000043261 Hevea brasiliensis Species 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 229920001400 block copolymer Polymers 0.000 claims description 8
- 229920003052 natural elastomer Polymers 0.000 claims description 8
- 229920001194 natural rubber Polymers 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 7
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 claims description 6
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 229920003051 synthetic elastomer Polymers 0.000 claims description 6
- 239000005061 synthetic rubber Substances 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000013638 trimer Substances 0.000 claims description 5
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical compound CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 claims description 3
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 claims description 3
- BEQGRRJLJLVQAQ-UHFFFAOYSA-N 3-methylpent-2-ene Chemical compound CCC(C)=CC BEQGRRJLJLVQAQ-UHFFFAOYSA-N 0.000 claims description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims 4
- 239000005060 rubber Substances 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000002474 experimental method Methods 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- VDMXPMYSWFDBJB-UHFFFAOYSA-N 1-ethoxypentane Chemical compound CCCCCOCC VDMXPMYSWFDBJB-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- BUWXUSLQPDDDSD-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-yloxy)butane Chemical compound CCC(C)(C)OC(C)(C)CC BUWXUSLQPDDDSD-UHFFFAOYSA-N 0.000 description 1
- PDBMKOUAWURVBE-UHFFFAOYSA-N 2-methyl-2-(2-methylpentan-2-yloxy)pentane Chemical compound CCCC(C)(C)OC(C)(C)CCC PDBMKOUAWURVBE-UHFFFAOYSA-N 0.000 description 1
- XIUZCZSOJYCCTG-UHFFFAOYSA-N 3-(butoxymethyl)heptane Chemical compound CCCCOCC(CC)CCCC XIUZCZSOJYCCTG-UHFFFAOYSA-N 0.000 description 1
- OMYMWDFOOFWXCW-UHFFFAOYSA-N 4-methyl-1-(4-methylpentoxy)pentane Chemical compound CC(C)CCCOCCCC(C)C OMYMWDFOOFWXCW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 241000746181 Therates Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50638774A | 1974-09-16 | 1974-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070335A true CA1070335A (fr) | 1980-01-22 |
Family
ID=24014365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,226A Expired CA1070335A (fr) | 1974-09-16 | 1975-08-11 | Resines derivees d'hydrocarbures de la piperylene et d'olefines tertiaires ramifiees a substituants methyle |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4098983A (fr) |
| JP (1) | JPS5159990A (fr) |
| BE (1) | BE833042A (fr) |
| CA (1) | CA1070335A (fr) |
| DE (1) | DE2536889A1 (fr) |
| FR (1) | FR2284620A1 (fr) |
| IT (1) | IT1041537B (fr) |
| NL (1) | NL7510883A (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3044592C2 (de) * | 1980-11-27 | 1982-09-23 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur katalytischen Polymerisation ungesättigter, aromatischer Kohlenwasserstoffe |
| US4514554A (en) * | 1983-02-23 | 1985-04-30 | Exxon Research And Engineering Co. | Petroleum resin and pressure sensitive adhesive formulations utilizing same as tackifier |
| US4683268A (en) * | 1986-02-18 | 1987-07-28 | Exxon Chemical Patents Inc. | Pressure sensitive adhesive using light color, low softening point petroleum hydrocarbon resins |
| US4677176A (en) * | 1986-02-18 | 1987-06-30 | Exxon Chemical Patents Inc. | Light color, low softening point petroleum hydrocarbon resins |
| CA1298026C (fr) * | 1986-02-18 | 1992-03-24 | Mary E. Ahner | Resines d'hydrocarbure non gazeux de couleur pale et a faible temperature de ramollissement et adhesifs auto-collants contenant ces resines |
| US4902766A (en) * | 1986-12-01 | 1990-02-20 | Exxon Chemical Patents Inc. | Liquid aliphatic resins |
| US5068490A (en) * | 1989-08-18 | 1991-11-26 | Amoco Corporation | BF3-tertiary etherate complexes for isobutylene polymerization |
| JP3119452B2 (ja) * | 1991-11-18 | 2000-12-18 | アモコ・コーポレーション | イソブチレン重合のためのbf▲下3▼・第三エーテレート錯体 |
| CN1037611C (zh) * | 1995-03-23 | 1998-03-04 | 中国科学院成都有机化学研究所 | 脂肪烃石油树脂的制造方法 |
| EP1900762A1 (fr) * | 2006-09-15 | 2008-03-19 | Rütgers Chemicals GmbH | Procédé de la préparation de résines d'hydrocarbures |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2753325A (en) * | 1952-12-22 | 1956-07-03 | Exxon Research Engineering Co | Resins from selected distillates |
| US3692756A (en) * | 1970-07-02 | 1972-09-19 | Goodyear Tire & Rubber | Hydrocarbon-derived resins having low softening point |
| US3928297A (en) * | 1971-06-08 | 1975-12-23 | Exxon Research Engineering Co | High molecular weight, high unsaturation isobutylene-conjugated diene copolymers |
| US3872064A (en) * | 1971-10-26 | 1975-03-18 | Goodyear Tire & Rubber | Liquid hydrocarbon derived resin |
| AT333027B (de) * | 1971-10-26 | 1976-10-25 | Goodyear Tire & Rubber | Verfahren zur herstellung eines harzes |
| US3966690A (en) * | 1973-05-04 | 1976-06-29 | The Dow Chemical Company | Modified hydrocarbon resins |
-
1975
- 1975-08-11 CA CA233,226A patent/CA1070335A/fr not_active Expired
- 1975-08-19 DE DE19752536889 patent/DE2536889A1/de not_active Ceased
- 1975-08-27 IT IT51084/75A patent/IT1041537B/it active
- 1975-09-02 FR FR7526846A patent/FR2284620A1/fr active Granted
- 1975-09-03 BE BE159723A patent/BE833042A/fr not_active IP Right Cessation
- 1975-09-16 NL NL7510883A patent/NL7510883A/xx not_active Application Discontinuation
- 1975-09-16 JP JP50112035A patent/JPS5159990A/ja active Granted
-
1976
- 1976-04-26 US US05/680,395 patent/US4098983A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL7510883A (nl) | 1976-03-18 |
| FR2284620A1 (fr) | 1976-04-09 |
| JPS5650897B2 (fr) | 1981-12-02 |
| FR2284620B1 (fr) | 1980-01-11 |
| DE2536889A1 (de) | 1976-04-01 |
| US4098983A (en) | 1978-07-04 |
| BE833042A (fr) | 1975-12-31 |
| IT1041537B (it) | 1980-01-10 |
| JPS5159990A (en) | 1976-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |